Abstract
In the title isoquinoline-1,3,4-trione derivative, C18H9NO5, the five-membered ring of the indane fragment adopts an envelope conformation with the nitrogen-substituted C atom being the flap. The planes of the indane benzene ring and the isoquinoline-1,3,4-trione ring make a dihedral angle of 82.06 (6)°. In the crystal, molecules are linked into chains extending along the bc plane via C—H⋯O hydrogen-bonding interactions, enclosing R 2 2(8) and R 2 2(10) loops. The chains are further connected by π–π stacking interations, with centroid-to-centroid distances of 3.9050 (7) Å, forming layers parallel to the b axis.
Keywords: crystal structure; isoquinoline-1,3,4-trione derivative; synthesis; hydrogen bonding; pharmacological properties
Related literature
For the biological activity of isoquinoline-1,3,4-triones, see: Chen et al. (2006 ▸); Du et al. (2008 ▸). For related isoquinoline-1,3,4-trione structures, see: Yu et al. (2010 ▸); Huang et al. (2013 ▸). For synthetic applications of isoquinoline-1,3,4-trione, see: Yu et al. (2010 ▸); Huang et al. (2011 ▸, 2013 ▸). For the synthesis of related compounds, see: Chen et al. (2006 ▸); Du et al. (2008 ▸); Ghalib et al. 2011 ▸; Schaber et al. 2004 ▸; Huang et al. (2013 ▸).
Experimental
Crystal data
C18H9NO5
M r = 319.26
Monoclinic,
a = 12.6080 (1) Å
b = 13.6849 (2) Å
c = 8.4467 (1) Å
β = 102.051 (1)°
V = 1425.27 (3) Å3
Z = 4
Cu Kα radiation
μ = 0.93 mm−1
T = 100 K
0.24 × 0.15 × 0.14 mm
Data collection
Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.808, T max = 0.879
9639 measured reflections
2597 independent reflections
2458 reflections with I > 2σ(I)
R int = 0.024
Refinement
R[F 2 > 2σ(F 2)] = 0.035
wR(F 2) = 0.093
S = 1.04
2597 reflections
217 parameters
H-atom parameters constrained
Δρmax = 0.27 e Å−3
Δρmin = −0.20 e Å−3
Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▸).
Supplementary Material
Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014025997/zl2607sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025997/zl2607Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014025997/zl2607Isup3.cml
. DOI: 10.1107/S2056989014025997/zl2607fig1.tif
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
A A x y z . DOI: 10.1107/S2056989014025997/zl2607fig2.tif
Crystal packing of the title compound, showing the C6–H6A⋯O2 and C7–H7A⋯O1 hydrogen bonding interactions (Symmetry codes: x, y, z + 1) as dashed lines incorporating 
(8) loops. Other H-atoms are omited for clarity.
x y z x y z x y z . DOI: 10.1107/S2056989014025997/zl2607fig3.tif
Crystal packing of the title compound, showing the C–H⋯O hydrogen bonding interactions (Symmetry codes: x, −y + 
, z − ; −x, y + , −z − ; −x, y − , −z − ) as dashed lines incorporating (10) loops. Other H-atoms are omited for clarity.
. DOI: 10.1107/S2056989014025997/zl2607fig4.tif
Reaction scheme for the title compound.
CCDC reference: 1036387
Additional supporting information: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (, ).
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C6H6AO2i | 0.95 | 2.54 | 3.4862(16) | 171 |
| C7H7AO1i | 0.95 | 2.51 | 3.1397(15) | 124 |
| C10H10AO5ii | 1.00 | 2.24 | 3.2022(15) | 161 |
| C13H13AO5iii | 0.95 | 2.37 | 3.2852(16) | 163 |
| C16H16AO4iv | 0.95 | 2.50 | 3.3596(17) | 150 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
Acknowledgments
RH and OS acknowledge Universiti Sains Malaysia (USM) for providing research facilities. CSCK thanks Universiti Sains Malaysia (USM) for a postdoctoral research fellowship. The authors extend their appreciation to The Deanship of Scientific Research at King Saud University for the research group project No. RGP VPP-207.
supplementary crystallographic information
S1. Chemical context
Urea has a complicated thermal behavior. It is thermally very liable to change. Thermal decomposition of urea under open reaction vessel conditions at temperatures in excess of 152 °C primarily gives cyanic acid (HNCO). HNCO on contact with additional urea in turn yields biuret which at a temperature of greater than 190 °C is liable to transform into cyanuric acid (Schaber et al., 2004). High-temperature thermal decomposition of cyanuric acid also gives cyanic acid again.
Heating of a mixture of ninhydrin and urea above the melting point of urea gives a mixture of 3a,8a-dihydroxy-1,3,3a,8a-tetrahydro- indeno[1,2-d]imidazole-2,8-dione (3) and the title compound 2-(1,3-dioxoindan-2-yl)-isoquinoline-1,3,4-trione (4) in about equal amounts, figure 4 (Ghalib et al. 2011). Compound 4 is most probably the product of reaction of nihyrin with cyanic acid. The formation of an isoquinoline-1,3,4-triones is of interest as some of these compounds have been known for their potent anticancer activity (Chen et al., 2006; Du et al. 2008). In continuation to our interest in the chemical and pharmacological properties of ninhydrin derivatives (Ghalib et al., 2011), we synthesized the title compound 4 as a precursor for the synthesis of potential chemotherapeutic agents (Chen et al., 2006).
S2. Structural commentary
In the title compound (Fig. 1), the study of torsion angles, asymmetric parameters and least squares planes reveals that the indane (C10–C12/C17/C18) ring adopts an envelope conformation with the nitrogen substituted C atom deviating by -0.104 (1) Å from the least-squares plane. The indane benzene ring (C12–C17) and the isoquinoline-1,3,4-trione ring exhibit a dihedral angle of 82.06 (6)°, suggesting they are almost perpendicular to each other.
S3. Supramolecular features
In the crystal structure, the molecules are connected into chains extending along the bc plane via intermolecular C–H···O hydrogen bonds (Table 1) enclosing R22(8) and R22(10) loops (Fig. 2 & 3). In addition, π–π interactions (Cg2···Cg3 = 3.9050 (7) Å; symmetry code: 1-x, 1-y, 1-z) stack the molecules into layers parallel to the b axis, where Cg2 and Cg3 are the centroids of the pyridine-2,3,6-trione and the benzene (C3–C8) rings respectively.
S4. Synthesis and crystallization
A dry mixture of ninhydrin (1) (1.78 g) and urea (2) (0.60 g) in molar ratio 1:1 was heated for 15 minutes to 150 °C above the melting point of urea (130–135 °C). The reaction mixture was cooled and then fractionally crystallized with an alcohol-chloroform (1:1) mixture to give colorless crystals of 3 as 3a,8a-dihydroxy-1,3,3a,8a-tetrahydro- indeno[1,2-d]imidazole-2,8-dione (yield 40%, M.P.: 220 °C) (Ghalib et al. 2011) and brownish crystals of the title compound 4 as 2-(1,3-dioxo-indan-2-yl)-isoquinoline-1,3,4-trione (yield 35%, m.p., 290 °C, Fig. 4).
S5. Refinement details
All the H atoms were positioned geometrically (C=H 0.93–0.98 Å) and refined using a riding model with Uiso(H) = 1.2 Ueq(C).
Figures
Fig. 1.
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
Fig. 2.
Crystal packing of the title compound, showing the C6–H6A···O2 and C7–H7A···O1 hydrogen bonding interactions (Symmetry codes: x, y, z + 1) as dashed lines incorporating R22(8) loops. Other H-atoms are omited for clarity.
Fig. 3.
Crystal packing of the title compound, showing the C–H···O hydrogen bonding interactions (Symmetry codes: x, -y + 1/2, z - 1/2; -x, y + 1/2, -z - 1/2; -x, y - 1/2, -z - 1/2) as dashed lines incorporating R22(10) loops. Other H-atoms are omited for clarity.
Fig. 4.
Reaction scheme for the title compound.
Crystal data
| C18H9NO5 | F(000) = 656 |
| Mr = 319.26 | Dx = 1.488 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 12.6080 (1) Å | Cell parameters from 6347 reflections |
| b = 13.6849 (2) Å | θ = 6.3–71.7° |
| c = 8.4467 (1) Å | µ = 0.93 mm−1 |
| β = 102.051 (1)° | T = 100 K |
| V = 1425.27 (3) Å3 | Block, orange |
| Z = 4 | 0.24 × 0.15 × 0.14 mm |
Data collection
| Bruker APEXII CCD diffractometer | 2458 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.024 |
| φ and ω scans | θmax = 72.0°, θmin = 6.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −15→14 |
| Tmin = 0.808, Tmax = 0.879 | k = −16→16 |
| 9639 measured reflections | l = −9→8 |
| 2597 independent reflections |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.5485P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 2597 reflections | Δρmax = 0.27 e Å−3 |
| 217 parameters | Δρmin = −0.20 e Å−3 |
Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.36681 (7) | 0.34686 (7) | −0.36897 (11) | 0.0226 (2) | |
| O2 | 0.56844 (7) | 0.37737 (7) | −0.18918 (11) | 0.0244 (2) | |
| O3 | 0.22076 (7) | 0.37449 (6) | 0.07501 (11) | 0.0212 (2) | |
| O4 | 0.14773 (7) | 0.52030 (7) | −0.25876 (13) | 0.0310 (3) | |
| O5 | 0.14677 (7) | 0.18880 (6) | −0.12358 (10) | 0.0208 (2) | |
| N1 | 0.29330 (8) | 0.35524 (7) | −0.14517 (12) | 0.0167 (2) | |
| C1 | 0.37928 (9) | 0.35678 (8) | −0.22453 (15) | 0.0171 (3) | |
| C2 | 0.49378 (10) | 0.37240 (8) | −0.11979 (15) | 0.0182 (3) | |
| C3 | 0.50578 (10) | 0.38012 (8) | 0.05673 (15) | 0.0173 (3) | |
| C4 | 0.60836 (10) | 0.39054 (9) | 0.15659 (16) | 0.0202 (3) | |
| H4A | 0.6710 | 0.3933 | 0.1108 | 0.024* | |
| C5 | 0.61838 (10) | 0.39680 (9) | 0.32253 (16) | 0.0219 (3) | |
| H5A | 0.6880 | 0.4043 | 0.3907 | 0.026* | |
| C6 | 0.52631 (10) | 0.39207 (9) | 0.39026 (16) | 0.0213 (3) | |
| H6A | 0.5339 | 0.3947 | 0.5045 | 0.026* | |
| C7 | 0.42389 (10) | 0.38360 (8) | 0.29149 (15) | 0.0191 (3) | |
| H7A | 0.3614 | 0.3817 | 0.3377 | 0.023* | |
| C8 | 0.41329 (10) | 0.37786 (8) | 0.12429 (15) | 0.0172 (3) | |
| C9 | 0.30286 (10) | 0.36955 (8) | 0.02176 (15) | 0.0172 (3) | |
| C10 | 0.18389 (9) | 0.34521 (9) | −0.24087 (15) | 0.0180 (3) | |
| H10A | 0.1894 | 0.3278 | −0.3539 | 0.022* | |
| C11 | 0.11456 (10) | 0.43817 (9) | −0.24898 (16) | 0.0210 (3) | |
| C12 | 0.00327 (10) | 0.40620 (9) | −0.24322 (16) | 0.0215 (3) | |
| C13 | −0.09105 (10) | 0.46146 (10) | −0.26425 (18) | 0.0276 (3) | |
| H13A | −0.0910 | 0.5291 | −0.2893 | 0.033* | |
| C14 | −0.18531 (11) | 0.41422 (10) | −0.2473 (2) | 0.0314 (3) | |
| H14A | −0.2510 | 0.4502 | −0.2610 | 0.038* | |
| C15 | −0.18544 (11) | 0.31468 (10) | −0.21033 (19) | 0.0315 (3) | |
| H15A | −0.2513 | 0.2842 | −0.2000 | 0.038* | |
| C16 | −0.09097 (11) | 0.25943 (10) | −0.18845 (18) | 0.0267 (3) | |
| H16A | −0.0910 | 0.1918 | −0.1629 | 0.032* | |
| C17 | 0.00336 (10) | 0.30685 (9) | −0.20540 (15) | 0.0201 (3) | |
| C18 | 0.11462 (9) | 0.26700 (8) | −0.18079 (14) | 0.0173 (3) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0203 (4) | 0.0298 (5) | 0.0183 (5) | −0.0022 (3) | 0.0056 (3) | −0.0011 (4) |
| O2 | 0.0176 (4) | 0.0350 (5) | 0.0221 (5) | −0.0004 (3) | 0.0075 (4) | 0.0005 (4) |
| O3 | 0.0169 (4) | 0.0267 (5) | 0.0214 (5) | −0.0016 (3) | 0.0072 (3) | −0.0031 (3) |
| O4 | 0.0215 (5) | 0.0205 (5) | 0.0501 (7) | −0.0025 (4) | 0.0055 (4) | 0.0081 (4) |
| O5 | 0.0218 (4) | 0.0175 (4) | 0.0219 (5) | 0.0011 (3) | 0.0019 (3) | −0.0010 (3) |
| N1 | 0.0137 (5) | 0.0192 (5) | 0.0172 (5) | −0.0005 (4) | 0.0031 (4) | −0.0007 (4) |
| C1 | 0.0180 (6) | 0.0152 (6) | 0.0189 (7) | 0.0001 (4) | 0.0055 (5) | 0.0008 (4) |
| C2 | 0.0169 (6) | 0.0160 (6) | 0.0222 (7) | 0.0003 (4) | 0.0055 (5) | 0.0006 (5) |
| C3 | 0.0180 (6) | 0.0149 (5) | 0.0190 (6) | 0.0000 (4) | 0.0043 (5) | 0.0012 (4) |
| C4 | 0.0180 (6) | 0.0196 (6) | 0.0234 (7) | −0.0004 (4) | 0.0054 (5) | 0.0014 (5) |
| C5 | 0.0185 (6) | 0.0224 (6) | 0.0226 (7) | −0.0017 (5) | −0.0004 (5) | 0.0007 (5) |
| C6 | 0.0250 (6) | 0.0207 (6) | 0.0180 (6) | −0.0017 (5) | 0.0036 (5) | −0.0004 (5) |
| C7 | 0.0206 (6) | 0.0178 (6) | 0.0202 (6) | −0.0010 (4) | 0.0069 (5) | −0.0003 (4) |
| C8 | 0.0181 (6) | 0.0138 (5) | 0.0198 (6) | −0.0005 (4) | 0.0039 (5) | 0.0002 (4) |
| C9 | 0.0180 (6) | 0.0146 (5) | 0.0198 (6) | −0.0006 (4) | 0.0060 (5) | −0.0006 (4) |
| C10 | 0.0157 (6) | 0.0203 (6) | 0.0174 (6) | −0.0002 (4) | 0.0024 (4) | 0.0001 (4) |
| C11 | 0.0177 (6) | 0.0207 (6) | 0.0237 (7) | −0.0003 (5) | 0.0022 (5) | 0.0039 (5) |
| C12 | 0.0178 (6) | 0.0202 (6) | 0.0257 (7) | −0.0012 (5) | 0.0031 (5) | 0.0000 (5) |
| C13 | 0.0203 (6) | 0.0192 (6) | 0.0423 (8) | 0.0017 (5) | 0.0042 (5) | 0.0014 (6) |
| C14 | 0.0177 (6) | 0.0261 (7) | 0.0497 (9) | 0.0029 (5) | 0.0058 (6) | −0.0034 (6) |
| C15 | 0.0188 (6) | 0.0264 (7) | 0.0508 (9) | −0.0049 (5) | 0.0107 (6) | −0.0036 (6) |
| C16 | 0.0222 (6) | 0.0189 (6) | 0.0398 (8) | −0.0028 (5) | 0.0083 (5) | −0.0010 (5) |
| C17 | 0.0183 (6) | 0.0195 (6) | 0.0225 (7) | −0.0007 (5) | 0.0039 (5) | −0.0019 (5) |
| C18 | 0.0177 (6) | 0.0180 (6) | 0.0157 (6) | −0.0019 (4) | 0.0025 (4) | −0.0035 (4) |
Geometric parameters (Å, º)
| O1—C1 | 1.2048 (15) | C7—C8 | 1.3927 (18) |
| O2—C2 | 1.2102 (15) | C7—H7A | 0.9500 |
| O3—C9 | 1.2136 (15) | C8—C9 | 1.4825 (17) |
| O4—C11 | 1.2080 (16) | C10—C18 | 1.5332 (16) |
| O5—C18 | 1.2088 (15) | C10—C11 | 1.5370 (16) |
| N1—C1 | 1.3886 (15) | C10—H10A | 1.0000 |
| N1—C9 | 1.4036 (16) | C11—C12 | 1.4802 (17) |
| N1—C10 | 1.4525 (15) | C12—C13 | 1.3890 (18) |
| C1—C2 | 1.5424 (16) | C12—C17 | 1.3966 (17) |
| C2—C3 | 1.4707 (17) | C13—C14 | 1.3863 (19) |
| C3—C4 | 1.3961 (17) | C13—H13A | 0.9500 |
| C3—C8 | 1.4016 (17) | C14—C15 | 1.398 (2) |
| C4—C5 | 1.3835 (18) | C14—H14A | 0.9500 |
| C4—H4A | 0.9500 | C15—C16 | 1.3901 (19) |
| C5—C6 | 1.3987 (18) | C15—H15A | 0.9500 |
| C5—H5A | 0.9500 | C16—C17 | 1.3883 (18) |
| C6—C7 | 1.3881 (18) | C16—H16A | 0.9500 |
| C6—H6A | 0.9500 | C17—C18 | 1.4787 (16) |
| C1—N1—C9 | 124.81 (10) | N1—C10—C18 | 114.97 (10) |
| C1—N1—C10 | 118.64 (10) | N1—C10—C11 | 114.32 (10) |
| C9—N1—C10 | 116.40 (10) | C18—C10—C11 | 103.57 (9) |
| O1—C1—N1 | 122.48 (11) | N1—C10—H10A | 107.9 |
| O1—C1—C2 | 120.34 (11) | C18—C10—H10A | 107.9 |
| N1—C1—C2 | 117.17 (10) | C11—C10—H10A | 107.9 |
| O2—C2—C3 | 124.14 (11) | O4—C11—C12 | 128.41 (12) |
| O2—C2—C1 | 117.35 (11) | O4—C11—C10 | 124.84 (11) |
| C3—C2—C1 | 118.51 (10) | C12—C11—C10 | 106.74 (10) |
| C4—C3—C8 | 120.06 (11) | C13—C12—C17 | 121.27 (12) |
| C4—C3—C2 | 120.40 (11) | C13—C12—C11 | 128.83 (12) |
| C8—C3—C2 | 119.54 (11) | C17—C12—C11 | 109.86 (11) |
| C5—C4—C3 | 119.71 (11) | C14—C13—C12 | 117.55 (12) |
| C5—C4—H4A | 120.1 | C14—C13—H13A | 121.2 |
| C3—C4—H4A | 120.1 | C12—C13—H13A | 121.2 |
| C4—C5—C6 | 120.23 (11) | C13—C14—C15 | 121.24 (12) |
| C4—C5—H5A | 119.9 | C13—C14—H14A | 119.4 |
| C6—C5—H5A | 119.9 | C15—C14—H14A | 119.4 |
| C7—C6—C5 | 120.36 (12) | C16—C15—C14 | 121.26 (12) |
| C7—C6—H6A | 119.8 | C16—C15—H15A | 119.4 |
| C5—C6—H6A | 119.8 | C14—C15—H15A | 119.4 |
| C6—C7—C8 | 119.63 (11) | C17—C16—C15 | 117.44 (12) |
| C6—C7—H7A | 120.2 | C17—C16—H16A | 121.3 |
| C8—C7—H7A | 120.2 | C15—C16—H16A | 121.3 |
| C7—C8—C3 | 119.98 (11) | C16—C17—C12 | 121.25 (11) |
| C7—C8—C9 | 118.45 (11) | C16—C17—C18 | 128.40 (11) |
| C3—C8—C9 | 121.57 (11) | C12—C17—C18 | 110.28 (10) |
| O3—C9—N1 | 118.63 (11) | O5—C18—C17 | 127.71 (11) |
| O3—C9—C8 | 123.28 (11) | O5—C18—C10 | 125.71 (11) |
| N1—C9—C8 | 118.09 (10) | C17—C18—C10 | 106.57 (10) |
| C9—N1—C1—O1 | −177.84 (11) | C1—N1—C10—C18 | 131.20 (11) |
| C10—N1—C1—O1 | −2.54 (16) | C9—N1—C10—C18 | −53.10 (13) |
| C9—N1—C1—C2 | 1.89 (16) | C1—N1—C10—C11 | −109.16 (12) |
| C10—N1—C1—C2 | 177.19 (9) | C9—N1—C10—C11 | 66.53 (13) |
| O1—C1—C2—O2 | 2.38 (17) | N1—C10—C11—O4 | 38.25 (18) |
| N1—C1—C2—O2 | −177.36 (10) | C18—C10—C11—O4 | 164.10 (13) |
| O1—C1—C2—C3 | −177.50 (11) | N1—C10—C11—C12 | −142.00 (11) |
| N1—C1—C2—C3 | 2.76 (15) | C18—C10—C11—C12 | −16.15 (13) |
| O2—C2—C3—C4 | −2.32 (18) | O4—C11—C12—C13 | 7.3 (2) |
| C1—C2—C3—C4 | 177.55 (10) | C10—C11—C12—C13 | −172.42 (13) |
| O2—C2—C3—C8 | 177.08 (11) | O4—C11—C12—C17 | −170.35 (14) |
| C1—C2—C3—C8 | −3.05 (16) | C10—C11—C12—C17 | 9.92 (14) |
| C8—C3—C4—C5 | 1.19 (17) | C17—C12—C13—C14 | −0.4 (2) |
| C2—C3—C4—C5 | −179.41 (11) | C11—C12—C13—C14 | −177.81 (14) |
| C3—C4—C5—C6 | 0.42 (18) | C12—C13—C14—C15 | 0.0 (2) |
| C4—C5—C6—C7 | −1.67 (19) | C13—C14—C15—C16 | 0.3 (2) |
| C5—C6—C7—C8 | 1.27 (18) | C14—C15—C16—C17 | −0.3 (2) |
| C6—C7—C8—C3 | 0.35 (17) | C15—C16—C17—C12 | −0.1 (2) |
| C6—C7—C8—C9 | −179.58 (10) | C15—C16—C17—C18 | 176.66 (13) |
| C4—C3—C8—C7 | −1.59 (17) | C13—C12—C17—C16 | 0.4 (2) |
| C2—C3—C8—C7 | 179.01 (10) | C11—C12—C17—C16 | 178.31 (12) |
| C4—C3—C8—C9 | 178.35 (10) | C13—C12—C17—C18 | −176.86 (12) |
| C2—C3—C8—C9 | −1.06 (16) | C11—C12—C17—C18 | 1.01 (15) |
| C1—N1—C9—O3 | 174.03 (10) | C16—C17—C18—O5 | −9.2 (2) |
| C10—N1—C9—O3 | −1.36 (15) | C12—C17—C18—O5 | 167.87 (12) |
| C1—N1—C9—C8 | −5.98 (16) | C16—C17—C18—C10 | 171.40 (13) |
| C10—N1—C9—C8 | 178.63 (10) | C12—C17—C18—C10 | −11.55 (14) |
| C7—C8—C9—O3 | 5.45 (17) | N1—C10—C18—O5 | −37.31 (17) |
| C3—C8—C9—O3 | −174.48 (11) | C11—C10—C18—O5 | −162.74 (12) |
| C7—C8—C9—N1 | −174.54 (10) | N1—C10—C18—C17 | 142.12 (10) |
| C3—C8—C9—N1 | 5.52 (16) | C11—C10—C18—C17 | 16.70 (12) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C6—H6A···O2i | 0.95 | 2.54 | 3.4862 (16) | 171 |
| C7—H7A···O1i | 0.95 | 2.51 | 3.1397 (15) | 124 |
| C10—H10A···O5ii | 1.00 | 2.24 | 3.2022 (15) | 161 |
| C13—H13A···O5iii | 0.95 | 2.37 | 3.2852 (16) | 163 |
| C16—H16A···O4iv | 0.95 | 2.50 | 3.3596 (17) | 150 |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z−1/2; (iv) −x, y−1/2, −z−1/2.
Footnotes
Supporting information for this paper is available from the IUCr electronic archives (Reference: ZL2607).
References
- Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
- Chen, Y. H., Zhang, Y. H., Zhang, H. J., Liu, D. Z., Gu, M., Li, J. Y., Wu, F., Zhu, X. Z., Li, J. & Nan, F. J. (2006). J. Med. Chem. 49, 1613–1623. [DOI] [PubMed]
- Du, J. Q., Wu, J., Zhang, H. J., Zhang, Y. H., Qiu, B. Y., Wu, F., Chen, Y. H., Li, J. Y., Nan, F. J., Ding, J. P. & Li, J. (2008). J. Biol. Chem. 283, 30205–30215. [DOI] [PMC free article] [PubMed]
- Ghalib, R. M., Hashim, R., Mehdi, S. H., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o1525. [DOI] [PMC free article] [PubMed]
- Huang, C. M., Jiang, H., Wang, R. Z., Quah, C. K., Fun, H. K. & Zhang, Y. (2013). Org. Biomol. Chem. 11, 5023–5033. [DOI] [PubMed]
- Huang, C. M., Yu, H. T., Miao, Z. R., Zhou, J., Wang, S. A., Fun, H. K., Xu, J. H. & Zhang, Y. (2011). Org. Biomol. Chem. 9, 3629–3631. [DOI] [PubMed]
- Schaber, P. M., Colson, J., Higgins, S., Thielen, D., Anspach, B. & Brauer, J. (2004). Thermochim. Acta, 424, 131–142.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Yu, H. T., Li, J. B., Kou, Z. F., Du, X. W., Wei, Y., Fun, H. K., Xu, J. H. & Zhang, Y. (2010). J. Org. Chem. 75, 2989–3001. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014025997/zl2607sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025997/zl2607Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014025997/zl2607Isup3.cml
. DOI: 10.1107/S2056989014025997/zl2607fig1.tif
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
A A x y z . DOI: 10.1107/S2056989014025997/zl2607fig2.tif
Crystal packing of the title compound, showing the C6–H6A⋯O2 and C7–H7A⋯O1 hydrogen bonding interactions (Symmetry codes: x, y, z + 1) as dashed lines incorporating (8) loops. Other H-atoms are omited for clarity.
x y z x y z x y z . DOI: 10.1107/S2056989014025997/zl2607fig3.tif
Crystal packing of the title compound, showing the C–H⋯O hydrogen bonding interactions (Symmetry codes: x, −y + , z − ; −x, y + , −z − ; −x, y − , −z − ) as dashed lines incorporating (10) loops. Other H-atoms are omited for clarity.
. DOI: 10.1107/S2056989014025997/zl2607fig4.tif
Reaction scheme for the title compound.
CCDC reference: 1036387
Additional supporting information: crystallographic information; 3D view; checkCIF report